4-(2-(1-methyl-1H-imidazol-2-ylthio)ethoxy)benzoic acid

ID: ALA3274635

PubChem CID: 12381181

Max Phase: Preclinical

Molecular Formula: C13H14N2O3S

Molecular Weight: 278.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1ccnc1SCCOc1ccc(C(=O)O)cc1

Standard InChI:  InChI=1S/C13H14N2O3S/c1-15-7-6-14-13(15)19-9-8-18-11-4-2-10(3-5-11)12(16)17/h2-7H,8-9H2,1H3,(H,16,17)

Standard InChI Key:  NMFNSUJGIXPBID-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 19 20  0  0  0  0  0  0  0  0999 V2000
    5.5464   -4.7069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9343   -5.4211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7337   -5.2716    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8373   -4.4647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1014   -4.1182    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3279   -5.8327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5538   -4.0718    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.2523   -4.4959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9689   -4.1030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6674   -4.5271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3839   -4.1342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0801   -4.5601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7962   -4.1679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8146   -3.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1111   -2.9260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3979   -3.3206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5315   -2.9533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2306   -3.3765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5484   -2.1363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  1  2  2  0
  3  4  1  0
  4  5  2  0
  5  1  1  0
  3  6  1  0
  4  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
 17 18  1  0
 17 19  2  0
 14 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3274635

   4-[2-(1-Methylimidazol-2-yl)sulfanylethoxy]benzoic acid

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 278.33

Molecular Weight (Monoisotopic): 278.0725

AlogP: 2.29

#Rotatable Bonds: 6

Polar Surface Area: 64.35

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.28

CX Basic pKa: 5.11

CX LogP: 1.51

CX LogD: -0.42

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.65

Np Likeness Score: -1.80

References

1. Tweit RC, Muir RD, Ziecina S..  (1977)  Nitroimidazoles with antibacterial activity against Neisseria gonorrhoeae.,  20  (12): [PMID:412966] [10.1021/jm00222a036]

Source

Source(1):

• Scientific Literature